PD166285   Click here for help

GtoPdb Ligand ID: 8183

Synonyms: PD-166285 | PD0166285 [5]
PDB Ligand
Compound class: Synthetic organic
Comment: PD166285 was originally reported as a tyrosine kinase inhibitor [1-2,4], and has subsequently been identified as an inhibitor of Wee1 [5] and Myt1 (PKMYT1) [3], two cyclin-dependent kinase (CDK) inhibitory kinases involved in regulating the cell cycle.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 72.28
Molecular weight 511.15
XLogP 6.53
No. Lipinski's rules broken 1
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Canonical SMILES CCN(CCOc1ccc(cc1)Nc1ncc2c(n1)n(C)c(=O)c(c2)c1c(Cl)cccc1Cl)CC
Isomeric SMILES CCN(CCOc1ccc(cc1)Nc1ncc2c(n1)n(C)c(=O)c(c2)c1c(Cl)cccc1Cl)CC
InChI InChI=1S/C26H27Cl2N5O2/c1-4-33(5-2)13-14-35-19-11-9-18(10-12-19)30-26-29-16-17-15-20(25(34)32(3)24(17)31-26)23-21(27)7-6-8-22(23)28/h6-12,15-16H,4-5,13-14H2,1-3H3,(H,29,30,31)
1. Klutchko SR, Hamby JM, Boschelli DH, Wu Z, Kraker AJ, Amar AM, Hartl BG, Shen C, Klohs WD, Steinkampf RW et al.. (1998)
2-Substituted aminopyrido[2,3-d]pyrimidin-7(8H)-ones. structure-activity relationships against selected tyrosine kinases and in vitro and in vivo anticancer activity.
J Med Chem, 41 (17): 3276-92. [PMID:9703473]
2. Panek RL, Lu GH, Klutchko SR, Batley BL, Dahring TK, Hamby JM, Hallak H, Doherty AM, Keiser JA. (1997)
In vitro pharmacological characterization of PD 166285, a new nanomolar potent and broadly active protein tyrosine kinase inhibitor.
J Pharmacol Exp Ther, 283 (3): 1433-44. [PMID:9400019]
3. Rohe A, Erdmann F, Bäßler C, Wichapong K, Sippl W, Schmidt M. (2012)
In vitro and in silico studies on substrate recognition and acceptance of human PKMYT1, a Cdk1 inhibitory kinase.
Bioorg Med Chem Lett, 22 (2): 1219-23. [PMID:22189141]
4. Trumpp-Kallmeyer S, Rubin JR, Humblet C, Hamby JM, Showalter HD. (1998)
Development of a binding model to protein tyrosine kinases for substituted pyrido[2,3-d]pyrimidine inhibitors.
J Med Chem, 41 (11): 1752-63. [PMID:9599227]
5. Wang Y, Li J, Booher RN, Kraker A, Lawrence T, Leopold WR, Sun Y. (2001)
Radiosensitization of p53 mutant cells by PD0166285, a novel G(2) checkpoint abrogator.
Cancer Res, 61 (22): 8211-7. [PMID:11719452]